ShoreTel Upgrade: Step-By-Step From Version 12.2 To 14.2/From Windows OS Version 2003 To 2012

I went through an upgrade from ShoreTel 12.2 to 14.2, directly.  However, I was changing hardware and also going to HyperV.  The customer wanted to make the move, even though I was not thrilled about it since this was the first version supported for HyperV.  I always say wait until the next version to work out the bugs, really in anything.  Just personal preference.  Below was my experience and the steps I took.  I hope its helpful.  Keep in mind, if I recall correctly, 12.2 is the lowest version you can go directly to 14.2 from.  If you have 12.1, you have to go to 12.2 first.

Contacted shoretel TAC to get 12.2 software (not available for general download)

NOTE*** If DHCP is on your 2003 box, you will need to move that to your 2012 box.

1. Double-click the script that stops all ShoreTel services - D:\Program Files\Shoreline Communications\ShoreWareServer\Scripts\hq_shoretel-stop-svcs.bat on the 2003 server.
2. Copy "shoreline data" folder to another location (copied backup over network to temp 2008 server)
3. disable NIC on voice vlan (its dual-homed).  Also, power it down, as you dont want it on the network when you put the new 2012 server in place.
4. Install 14.2 on new server (2012 server) (Just doing this while waiting on download of 12.2 from FTP server from ShoreTel)  Make sure you name it the same as the 2003 server.
5. install Shoretel 12.2 on 2008 box. (Just FYI, I had to install the OS on a PC.  The customer didnt have a 2008 server for me to use, so we had to install this on an old PC just as a stepping stone).
6.  Change name on 2008 server and IP address to match the 2003 box.  (I took off network for this)
7.  Turn Windows firewall off.  It wont install with this on.
8.  Install Roles on 2008 server.(Check the Application Server and Web Server (IIS) check boxes and select all relevant features listed: p190 in 14.2 install guide:
9.  As I install the Shoretel software, it wants to Install visual C++ on 2008 server.
10.  Reboot.
11.  Run \Program Files\Shoreline Communications\ShoreWareServer\Scripts\hq_shoretel-stop-svcs.bat on the 2008 server.
12. verify all shoretel services did actually stop.
13. Rename the Shoreline Data folder and Copy the original 2003 Shoreline Data folder into place.
14. start shoretel services again on 2008 box. (Run \Program Files\Shoreline Communications\ShoreWareServer\Scripts\hq_shoretel-start-svcs.bat)
15.  Verify they are all started.
16.  Copy 14.2 software onto 2008 server.
17.  Extract and run 14.2 install of Shoretel software.
18.  reboot when install is complete.
19.  Login and verify install version.
20.  Stop shoretel services on 2008 server with hq bat file.
21.  Backup shoreline data folder again, so that we can import into the 2012 server.
22.  Copy Shoreline Data folder to the new 2012 server.
23.  install shoretel 14.2 software just like you did on the 2008 server, including roles and features needed, and other preinstall items located in the install manual.
24.  When install is complete, reboot.
25.  Login and stop all ShoreTel services with the hq stop bat file.
26.  Copy the shoreline data folder into the new 2012 server, replacing the shoreline data folder from the new install.
27.  Start ShoreTel services after the copy is complete.
28.  This is a HyperV environment for this install, so make sure the mac address on the virtual NIC is the same was the 2003 server it came from, if you plan on decommissioning the 2003 server (or disabling that NIC).  If this is going on a new server with a different MAC address, then you will have to relicense the server with the new MAC address. (NOTE*** I did have to relicense even though it used the same MAC address.  Not sure why.  Didn't care, just relicensed and completed project.

Below is the 2008 stepping stone I used.  Just made me laugh.  One of my server engineers got me a thumb drive ready with a bootable 2008 copy.  Very nice of him to do for me.  Thanks Justin for doing that for me.  You can also see another senior engineer is working on a Palo Alto project.